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Vacation Rentals & Homes in Sag Harbor

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192 homes

Beech Tree Cottage

Sag Harbor cottage

2 bedrooms / 1 bathroom / sleeps 4

“Loved this place” This is the perfect little getaway for those who wish to avoid the pretentiousness of East Hampton and Southampton and still enjoy everything that the Hamptons has to offer. Best things - very cute little cottage. Good enough space with off-street parking. The ability to walk into Sag Harbor village in a few mins is a massive plus. Stephen and Emma are so nice and great neighbors if there are any issues. Would definitely recommend this place to anyone.

Price per night from

$686

Sag Harbor Home w/ Pool - 5 Mins to Downtown!

Sag Harbor house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,244

East Hampton/Sag Harbor Village Fringe

Sag Harbor house

6 bedrooms / 7 bathrooms / sleeps 12

Price per night from

$3,436

Elegant Designer Hamptons Retreat in Sag Harbor

Sag Harbor house

5 bedrooms / 7 bathrooms / sleeps 12

“Excellent vacation!” Beautifully decorated Designer home was fully furnished with great touches you would expect in a high end rental--soft linens and towels, mini ipods in docking stations around the house, fully stocked kitchen, fabulous pool and backyard. We loved the location!

Responds fast! avg. 2 hours 2 minutes

Price per night from

$3,266

Sag Harbor Village Fringe, Great Location

Sag Harbor house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$2,286

ROMANTIC LUXURY RETREAT WITH POOL & WATER VIEWS, 1 MILE FROM SAG HARBOR VILLAGE

Sag Harbor house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$995

Hampton's Paradise sag Harbor, Southampton

Sag Harbor house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,143

Village traditional on a quiet cul de sac

Sag Harbor house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,291

The Seashell House

Sag Harbor house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$974

6BR Private Home In Sag Harbor / Southampton With Pool & Jacuzzi

Sag Harbor house

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 21 minutes

Price per night from

$317

Beautiful Guest House Waits For You - Hamptons - Sag Harbor

Sag Harbor guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$286

no longer avail property Sold !

Sag Harbor cottage

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,029

Great 4 bedroom family home walking distance to the beach and village

Sag Harbor house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,139

Why Share? Beautiful guest house! Hamptons - Sag Harbor

Sag Harbor guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$430

Great rentals within 20 miles that match your search

North Fork House with Private Beach Access

East Marion house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 24 minutes

Price per night from

$342

Ready for Summer 2021

Southampton house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,715

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,258

Hampton Bays, south of 27A

Hampton Bays house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 55 minutes

Price per night from

$458

Waterfront Southampton Gem! Sailboat On Grounds - Travertine patio and Hot Tub

Water Mill house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$778

East Hampton shingle style home

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$858

North Fork 5 bed room home with forever farm view

Aquebogue house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$458

Montauk Ocean View Retreat-Rental Registry #16-950

Montauk house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,143

Amagansett Estate 3 BR 60ft Pool

Amagansett house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,029

Beautiful Estate home in the Hamptons, New York

Water Mill villa

7 bedrooms / 7 bathrooms / sleeps 10

Price per night from

$6,858

Bishops Pond Southampton NY

Southampton townhouse

4 bedrooms / 10 bathrooms / sleeps 8

Price per night from

$147

SOUTHAMPTON NEW YOK LUXURY RENTAL

Southampton house

4 bedrooms / 11 bathrooms / sleeps 8

Price per night from

$2,042

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,200

Southampton Water Front Retreat

Southampton cottage

4 bedrooms / 10 bathrooms / sleeps 10

Price per night from

$1,906

Cottage by the Sea

Montauk cottage

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,142

Amagansett House with Pool near Village & Beach

Amagansett house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,307

East Hampton Dream House 'Serendipity' - Great Buy

East Hampton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$572

Hamptons Summer Getaway

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$686

Serene & Private East Hampton Summer Rental w/pool

East Hampton house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$816

East Hampton Village Classic , South of Highway

East Hampton house

7 bedrooms / 9 bathrooms / sleeps 12

Price per night from

$4,082

Montauk Oceanfront Estate

Montauk manor house

5 bedrooms / 8 bathrooms / sleeps 10

Price per night from

$11,430

Dream house vacation on the Long Island Sound

Orient house

5 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 52 minutes

Price per night from

$1,086

Elegance,Privacy, French Farm House

East Hampton farmhouse

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,088

North Fork cottage getaway with private beach

Mattituck cottage

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 50 minutes

Price per night from

$311

Viewing 38 of 192
rentals in Sag Harbor

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About Sag Harbor

Sag Harbor is historic hamlet with a real maritime vibe. If you're hoping to experience a unique culture, a world away from normal life, this quirky little resort is certainly an option for you. FlipKey has a great selection of homes to choose from. Book today to secure your Sag Harbor stay.

About Sag Harbor

Sag Harbor is a small village located in Suffolk County, New York and has an extremely rich history which tourists are still eager to discover to this day. The first settlers arrived in the 1600s, and by the 1800s became one of the busiest ports in the world, still famed for its marine heritage.

Thanks to years of preservation and care, the majority of the architecture from the 18th and 19th centuries still remains, which include the likes of Greek Revival Houses and Victorian homes for the rich.

The area within and around Sag Harbor has a great deal of nature, as well as many endangered species such as the eastern tiger salamander. Nature preserves in Sag Harbor include Barcelona Neck Preserve, Sag Harbor Woods Preserve and Cilli Farm. Here, you may be able to spot mammals such as the white-tailed deer, red fox, eastern coyote, mink and a variety of bat species.

What to do

If you're interested in seeking out the cultural sights of the region, why not visit the Sag Harbor Fire Department Museum? Built in 1833, this building was created due to four severe blazes which broke out in the 1800s. Now, it serves as a museum and displays a wide range of fire equipment and other interesting pieces to view.

There's also the Sag Harbor Whaling and Historical Museum, located in an 1845 building. Here, you can explore displays of marine heritage with boat displays, models and furnishings as well as special exhibits.

If you're looking to see more of the area, you may decide on taking a trip to the local rocky beach known as Foster Memorial Beach. Or, if you're looking for a taste of adventure, the most popular activities here are kayaking and boating out to Long Island. You will enroll in a two-day course which is ideal for beginners.

Top Sea Harbor travel tips

If you're looking to find a cheaper alternative than traveling to Suffolk County by plane, there is a bus which departs from Manhattan and will drop you off at Sag Harbor. The round-trip fare is just $53 per person.

It would be advised to have a car to get around Sag Harbor, due to the remoteness of the town. This would also be advised if you plan on exploring the other local areas or are hoping to venture out further.

The peak season to travel to this particular region is between May-September, so always book far in advance.

Sag Harbor is the idealized quiet town you may have always wished to escape to; especially if you live in a busy city. Here, you can explore history culture and even try your hand at water-sports if you dare... Book your Sag Harbor vacation rental with FlipKey to start your next trip.

Top Destination reviews

Beech Tree Cottage
A home from home

I stayed with two friends, their 15 month old and two week old in Beech Tree Cottage in June and we had a great time. The cottage has a very comfortable, cosy feel to it and had everything we needed. The location is perfect as we were close to town and it was easy to get around by car to explore the area. The owners are keen to point out that there is no bath and that the spiral staircase is narrow, but this didn't prove a problem for us for a two-night stay. We were only sorry not to meet our hosts during our short stay. Highly recommended.see more
Elegant Designer Hamptons Retreat in Sag Harbor
If it has to be terrific, this is the place to rent...

I can't say enough good things about our stay in this lovely Sag Harbor home. It's beautifully furnished, absolutely clean, and situated in a handsome gated community just outside Sag Harbor. The owner was helpful, flexible and really couldn't have done more to make sure our stay was enjoyable. … see more

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